JPS6348280B2 - - Google Patents
Info
- Publication number
- JPS6348280B2 JPS6348280B2 JP55122501A JP12250180A JPS6348280B2 JP S6348280 B2 JPS6348280 B2 JP S6348280B2 JP 55122501 A JP55122501 A JP 55122501A JP 12250180 A JP12250180 A JP 12250180A JP S6348280 B2 JPS6348280 B2 JP S6348280B2
- Authority
- JP
- Japan
- Prior art keywords
- methyldichlorophosphane
- reaction
- methyl
- mol
- phosphorus trichloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- CDPKWOKGVUHZFR-UHFFFAOYSA-N dichloro(methyl)phosphane Chemical compound CP(Cl)Cl CDPKWOKGVUHZFR-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims abstract description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 19
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 19
- SGGKZWABPPXBNE-UHFFFAOYSA-N 3-[chloro(methyl)phosphoryl]propanoyl chloride Chemical class CP(Cl)(=O)CCC(Cl)=O SGGKZWABPPXBNE-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 27
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract description 26
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000012043 crude product Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 3
- -1 2-chloroformylethyl-methyl-phosphinic acid Chemical compound 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000011345 viscous material Substances 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- 229910019213 POCl3 Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/34—Halides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792936609 DE2936609A1 (de) | 1979-09-11 | 1979-09-11 | Verfahren zur herstellung von 2-chlorformylethyl-methyl-phosphinsaeurechloriden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5645493A JPS5645493A (en) | 1981-04-25 |
| JPS6348280B2 true JPS6348280B2 (de) | 1988-09-28 |
Family
ID=6080520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12250180A Granted JPS5645493A (en) | 1979-09-11 | 1980-09-05 | Manufacture of 22chloroformylethyllmethyll phosphinic chloride |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4318865A (de) |
| EP (1) | EP0026815B1 (de) |
| JP (1) | JPS5645493A (de) |
| AT (1) | ATE1099T1 (de) |
| CA (1) | CA1143382A (de) |
| DE (2) | DE2936609A1 (de) |
| ZA (1) | ZA805580B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2990953B2 (ja) * | 1991-08-09 | 1999-12-13 | 堺化学工業株式会社 | ホスフィニルカルボン酸誘導体の製造方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52106821A (en) * | 1976-03-05 | 1977-09-07 | Hoechst Ag | Process for manufacturing *22*halogenformyl** vinyl**organyllphosphine acid halogenide |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1063628B (it) * | 1975-07-03 | 1985-02-11 | Hoechst Ag | Procedimento per la produzione di alogenuri di acidi beta alogenoformil etil fosfinici |
| US4042888A (en) * | 1976-02-26 | 1977-08-16 | Westinghouse Electric Corporation | Signal amplifier apparatus with fail-safe limited gain |
| GB1533200A (en) * | 1976-06-30 | 1978-11-22 | Hoechst Ag | Production of methyldichlorophosphane |
| GB1562008A (en) * | 1976-07-14 | 1980-03-05 | Hoechst Ag | Production of methyldichlorophosphine |
-
1979
- 1979-09-11 DE DE19792936609 patent/DE2936609A1/de not_active Withdrawn
-
1980
- 1980-07-16 AT AT80104159T patent/ATE1099T1/de active
- 1980-07-16 DE DE8080104159T patent/DE3060469D1/de not_active Expired
- 1980-07-16 EP EP80104159A patent/EP0026815B1/de not_active Expired
- 1980-08-06 CA CA000357710A patent/CA1143382A/en not_active Expired
- 1980-09-05 JP JP12250180A patent/JPS5645493A/ja active Granted
- 1980-09-08 US US06/185,154 patent/US4318865A/en not_active Expired - Lifetime
- 1980-09-10 ZA ZA00805580A patent/ZA805580B/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52106821A (en) * | 1976-03-05 | 1977-09-07 | Hoechst Ag | Process for manufacturing *22*halogenformyl** vinyl**organyllphosphine acid halogenide |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1143382A (en) | 1983-03-22 |
| DE2936609A1 (de) | 1981-04-02 |
| DE3060469D1 (en) | 1982-07-15 |
| JPS5645493A (en) | 1981-04-25 |
| EP0026815A1 (de) | 1981-04-15 |
| US4318865A (en) | 1982-03-09 |
| EP0026815B1 (de) | 1982-05-26 |
| ZA805580B (en) | 1981-09-30 |
| ATE1099T1 (de) | 1982-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8097749B2 (en) | Isothermal process for phosphoromonochloridite synthesis | |
| HU184790B (en) | Process for preparing 2-chloro-alkyl-propionates by means of the chlorination of alkyl-lactate | |
| US1945183A (en) | Manufacture of alkoxy derivatives of phosphorous acid chlorides | |
| US4595541A (en) | Process for the preparation of trifluoroacetic anhydride | |
| JPS6348280B2 (de) | ||
| EP0813515B1 (de) | Verfahren zur Herstellung von Estern der Stilbendicarbonsäure und Verfahren zur Herstellung von p-(Chlormethyl)-Benzoesäure | |
| JPS5835171B2 (ja) | ベンゾインエ−テルノセイゾウホウ | |
| US3631067A (en) | Preparation of coumarin | |
| JPH0320370B2 (de) | ||
| JPH06172373A (ja) | ６−クロロ−（６Ｈ）−ジベンズ［ｃ，ｅ］［１，２］− オキサホスホリンの製造方法 | |
| US2434507A (en) | Z-otloro-j-iminobutyronitrile | |
| CA1055959A (en) | Continuous production of 2,5-dioxo-1-oxa-2-phospholanes | |
| US4296047A (en) | Continuous preparation of phosphoric acid alkyl ester dichlorides | |
| US3535351A (en) | Alkyl cyanoperfluoroalkanoates | |
| US4172845A (en) | Production of [2-(halogenoformyl)-vinyl]-organyl phosphinic acid halides | |
| US3931333A (en) | Production of halogen-containing tertiary phosphine oxides | |
| US4367349A (en) | Liquid phase synthesis of hexafluoroisobutylene | |
| JPH0725708B2 (ja) | パーフルオロアルキルブロミドの合成 | |
| US2603660A (en) | Preparation of dialkylalkanamides | |
| US4224241A (en) | Production of halogenomethylphosphinic acid halides | |
| EP1810975A1 (de) | Verfahren zur herstellung von phosphonat mit alkoholischer hydroxygruppe | |
| US3555074A (en) | Process for producing an insecticide | |
| US3642867A (en) | Process for the preparation of a 1 2-bis(4-carboalkoxyphenoxy)ethane | |
| GB2305432A (en) | Method of purifying 1,3-bis(3-aminopropyl)-1,1,3,3-tetraorganodisiloxane | |
| US3632831A (en) | Synthesis of dialkyl 4 4'-biphenyldicarboxylates |